Markets and property types
Why Single-Family Rentals Stopped Working (And What to Buy Instead)
Single-family wasn't built to be an investment. Here's why the math no longer works, and why 5-to-50-unit multifamily is easier to buy, fund, and scale.
There are some glaring problems with single-family investing right now. Not because single-family never works, but because the ways you have to make it work are neither sustainable nor scalable. In this one I lay out exactly where the model breaks down, then propose a business plan that I think works much better and is a lot simpler.
Why listen to me on this? I've done a whole lot of these businesses. I've done Airbnb. I've done short-term. I've bought duplexes: 11 of them in my portfolio, and today I own almost none of them. I've done the small property thing and I've done large properties. I also own the Robin Hood Village Resort, an 18-cabin waterfront resort. Short-term, long-term, multifamily, single-family: I've done it all. If you want to know how to make the most money with the least amount of effort, and honestly have the most fun doing it, this is where I'd point you.
Related reading: Why I Bought a $5.4M Resort Instead of an Airbnb
"Rentals Don't Cash Flow Anymore" Is Nonsense
You've seen this all over the internet: a whole bunch of influencers saying rentals no longer work, you just can't buy for cash flow anymore.
That's absolutely BS. I would never in a million years buy a deal that doesn't cash flow day one. I tried it. Don't like it.
Every time you buy a rental property, it needs to increase your income. That way every time you close, you get a raise for the rest of your life. Repeat that again and again and you end up with a ton of money coming in relatively passively every single month. I'll tell you from the other end of it: that feels pretty good. It's nice not to worry about the money coming in, with minimal hours spent on acquisition and management.
So cash flow is very much available. The problem isn't the market. The problem is the asset class most people start in.
Single-Family Was Never Designed to Be an Investment
This is the most important point. A single-family house is designed to be a house for people who want to live at the property.
People want to buy houses. That has always been the American dream. Yes, we're slowly shifting to a renter nation, but we're not there yet. The core dream is still: save up, one day buy a house. As someone who has owned multiple houses I've lived in, it's fun to own your own space. It's fun to design your own space, especially as people get to the age where they want to start a family. There are advantages to home ownership that the "just always rent" financial classes don't teach you. Sometimes you just want to own where you live.
Which means the pricing of single-family is set by people who want to own where they live. You are not the natural buyer of that asset: you're a bidder in someone else's market.
The Margin Games Everyone Uses to Compensate
Because cash flow is so hard to find in an asset never designed for cash flow, people have invented ways to push the margin:
- Airbnb. The big one for years, though it's slowly dying. There's still a lot of it.
- Mid-term rentals. These are actually working very well right now. I think it's the best single-family strategy currently available: higher margin, mid-term leases, and there are a bunch of different ways to source them.
- Co-living. My least favorite. You essentially make everyone roommates. It's management-heavy and difficult to scale, but it does push income much, much higher on an individual house.
Here's the trap. Because people are finding ways to make more money with these houses, people will pay more money for these houses. So if you're doing a conventional purchase, you're competing both against people who want to live there and call it their own, and against people running a higher-yield strategy than you are. Other buyers are willing to pay more than you for the same property. That's why you no longer cash flow in single-family in most markets.
The only places we consistently see cash flow are areas with declining population, where you can buy so cheap that the numbers finally work.
Ask yourself whether you want an entire portfolio of cheap properties in declining towns. Is the goal to be the best slumlord in the country? I don't think so. That's not a business I'm interested in, and it's not rewarding.
And because those properties are inexpensive, you have to do a ton of transactions. If each deal adds $100 or $200 a month, and you're trying to get to $10,000 a month, you're buying again and again and again. Then one disaster at one property wipes out most of your cash flow.
So single-family fails for a series of reasons: too many transactions to get from A to B, the wrong competition, and a business that was never designed to be a business.
Argument One: Bigger Deals Are Easier to Fund
It's easy to get stuck in the mindset that a smaller deal costs less money, so it's easier to get into. Let me dispel that right now.
The bigger the deal, typically the easier the raise: until you get into multi-million-dollar raises. It's more attractive for more people to invest in something bigger than they could do on their own. So your actual ability to buy with low to no money out of pocket increases dramatically.
Over my last 32 transactions, it has been much easier to raise a million dollars for a fantastic cash-flowing deal than for a speculative single-family house. Your investor pool is much larger. A million dollars in multifamily is easier to find than $100,000 in single-family.
You create an opportunity, and the cash flow and upside of that opportunity is what attracts capital. If you're stuck thinking "it costs less, so I need to find less money," stop doing that immediately.
To be clear about the size I'm talking about: mid-size multifamily or a boutique hotel. Five to 50 units. Not Titanic properties. Not the 300-unit mega complex that just got built down the street. Something built in the '80s, '90s, or early 2000s, five to 50 units at the most. That's the sweet spot where you can operate. Low capital raises, not capital intensive, attractive to investors, and designed very specifically to cash flow.
Argument Two: You Only Have to Win Once a Quarter
I only need to succeed about once a quarter. Really, twice a year would still do it.
If you bought a couple of 25-unit buildings and each one cash flows three or four thousand dollars a month, you've added $8,000 a month for life, and it adjusts with inflation: so on average it goes up a little every year.
If two transactions get me to eight or ten thousand a month, and I do that consistently, once every half year or once a quarter, maybe up to four deals a year, you start accumulating hundreds of rental units without doing a lot of volume. The sustainability, the management, the systems: you can build a business that spits out tens of thousands of dollars instead of scraping your way to your next five or ten thousand over multiple years with tons of transactions and a lot of headache.
Argument Three: You Negotiate Against Numbers, Not Problems
In single-family, you tend to get a whole lot of problems in small properties bought from small mom-and-pop owners. They're usually selling because there's a problem with the property. They bought it to be passive, they ran it incorrectly, and it's not passive at all. You're coming in to fix substantial problems. That's the majority of the deals we see.
Which means to push the margin you have to build an ADU and become a little micro-developer, or switch the use to Airbnb and spend the time, money, and risk to get it there.
On multifamily, you negotiate based on the cash flow today and the future upside, which is just a function of how well you run the property. Appraisals are done on your net operating income, not on what your neighbors just sold for. Your ability to find debt products, to find capital, the transaction volume: everything is easier.
And at the end of the day, walk around a 25-unit or 50-unit building and feel "I own this," versus walking in front of a random house somewhere you'll probably never go inside again. It's a different feeling. It's a bigger business, it's more rewarding, and you're providing housing to people who want to rent. You're not taking homes off the market and competing with everyone else.
Key Takeaways
- Cash flow still exists. I'd never buy a deal that doesn't cash flow day one: the asset class is the problem, not the market.
- Single-family pricing is set by owner-occupants and by operators running Airbnb, mid-term, or co-living. You're outbid on every one.
- Where single-family still cash flows is mostly declining-population markets, and that's a portfolio of cheap buildings and constant transactions.
- Raising a million dollars for a strong cash-flowing multifamily deal is easier than raising $100,000 for a speculative house.
- Five to 50 units, built '80s through early 2000s, is the sweet spot: low raises, real cash flow, manageable.
- Two to four deals a year gets you to tens of thousands a month. You don't need volume, you need the right size.
If 2026 is your year to get into real estate and you were planning to buy your first investment house, here's my challenge: increase it by five units. Do something commercial. It doesn't have to be huge: buy a 5-plex, buy a 12-plex. You'll find it easier to manage, with more availability, more cash flow, easier money, and an easier close.
Watch the full episode above for the whole case laid out end to end. If you want help getting there, there's a free multifamily course on the site to get started, a free Skool community that comes with a deal calculator, and mentorship details if you'd rather have direct coaching on a live deal.
Read the episode transcript
0:00 There are some glaring problems with 0:02 single [music] family investing right 0:03 now. On today's episode, I'm going to go 0:05 over what the biggest hurdles are, and 0:07 I'm going to make a case for you on why 0:09 you should shift your business model. 0:10 Not because single family never works, 0:12 but the ways that you make it work are 0:15 not sustainable and not scalable. I'm 0:17 going to go into this in detail, and I'm 0:19 going to propose a business plan that 0:20 will work much, much better for you on 0:23 this episode. And I think it's going to 0:24 be a lot simpler. So, if you're looking 0:25 at building single family, duplex, 0:27 triplex, forplex, maybe it's the price 0:29 point, maybe there's some angle or 0:31 gimmick that you found online where 0:33 you're like, "Hey, I think I can scale 0:34 this and push my margin." I'm going to 0:36 make a case that is going to save you a 0:38 lot of time and ultimately make you a 0:40 lot more money. Oh, by the way, welcome 0:41 to the channel. Why would you listen to 0:42 me? Well, I've done a whole lot of these 0:44 businesses. I've done Airbnb. I've done 0:46 short-term. I've bought duplexes. In 0:48 fact, I've bought 11 duplexes in my 0:50 portfolio. Today, I own almost none of 0:52 them. I've done the small property 0:54 thing. I've done large properties. I've 0:56 also done boutique resort. I own the 0:58 Robin Hood Village Resort at 18 cabin 1:00 resort with waterfront. So, when you're 1:01 talking short-term, long-term, multif 1:03 family, single family, I have done it 1:06 all. I will tell you what works. If you 1:08 want to know how to make the most money 1:10 with the least amount of effort and 1:11 ultimately, I think have the most fun. 1:13 I'm going to show you how to do that 1:15 exactly in this episode. So, let's dive 1:18 right into it. the glaring issues. And 1:20 you've probably seen this all over 1:22 online. There's a whole bunch of 1:23 influencers that are going, "Oh, rentals 1:25 no longer work. You just can't buy for 1:27 cash flow anymore." Well, first of all, 1:29 that's absolutely BS. I would never in a 1:31 million years buy a deal that doesn't 1:33 cash flow day one. Tried it. Don't like 1:36 it. Every time that you buy a rental 1:38 property, it needs to increase your 1:40 income. That way, every time you close, 1:42 you get a raise for the rest of your 1:43 life. If you repeat this again and again 1:44 and again, ultimately, you end up with a 1:46 ton of money coming in relatively 1:49 passively every single month. If that 1:51 sounds good to you, I'll tell you, being 1:53 on the other end of this, it feels 1:55 pretty good. It's nice to not have to 1:57 worry about the money coming in and 1:59 minimal hours of working on acquisition 2:01 and management. I really like it. I 2:04 highly recommend. So, why doesn't single 2:06 family work? Well, the first thing, and 2:07 I think the most important, single 2:09 family is not designed to be an 2:11 investment. It's designed to be a house 2:13 for people who want to live at the 2:16 property. 2:17 People want to buy houses. This has 2:19 always been the American dream. Now, 2:20 yes, we're slowly shifting to a renter 2:22 nation, but we're not there yet. The 2:24 core American dream is still, hey, I 2:26 want to save up one day, buy a house. 2:28 And as someone who's owned multiple 2:29 houses that I've lived in, it's fun to 2:32 own your own space. It's fun to get to 2:33 design the own space, especially as 2:35 people get into the age where they want 2:36 to start a family. There's a lot of 2:38 advantages to home ownership that they 2:40 don't teach you on the financial classes 2:42 or the like, oh, just always rent your 2:44 space. Sometimes you just want to own 2:46 where you live. And I think that's a lot 2:48 of Americans, which means the pricing is 2:51 designed for people who want to own 2:52 where they live. What else is single 2:54 family designed for over the past few 2:56 years? Because of the difficulty in 2:58 getting cash flow in single family that 3:00 was never designed for cash flow, people 3:02 have found different ways to push the 3:04 margin. Airbnb was the big one, though 3:07 it's slowly dying. There's still a lot 3:09 of Airbnb. There's mid-term rentals that 3:11 are currently actually working very well 3:13 as a strategy for a lot of people. I 3:15 actually think it's the best single 3:16 family strategy currently available. 3:18 Higher margin, midterm leases, and 3:21 there's a bunch of different ways to get 3:22 them. And then you have the people who 3:24 are doing the co-living. It's my least 3:26 favorite way to push the margin, but 3:28 they essentially make everyone 3:29 roommates. It's managementheavy. It's 3:32 difficult to scale, but it's a way where 3:33 you can push that income much much much 3:35 higher for an individual single family 3:37 property. Because of this, people are 3:40 finding ways to make more money with 3:41 them, which means people will pay more 3:43 money. So, if you do conventional 3:45 purchase and you're competing with 3:47 people who want to live in the house and 3:48 call it their own, or people who have 3:50 other methods to make a higher yield 3:52 than you, other people are willing to 3:54 pay more than you are for the same 3:56 property. Therefore, you no longer can 3:59 cash flow in single family in most 4:00 markets. The only places that we're 4:02 consistently seeing cash flow is areas 4:04 with declining population. You can buy 4:05 so cheap that you can get to cash flow. 4:09 Now, you have to ask yourself, do you 4:10 want to have an entire portfolio full of 4:12 cheap properties? Is your goal, hey, I 4:15 want to have a cheap I want to be the 4:17 best slum lord in the country. I don't 4:19 think so. At least that's not a business 4:20 I'm interested in. Not rewarding. And 4:22 also, because they're inexpensive, you 4:24 have to do a ton of transactions. If 4:26 you're talking about adding like a $100, 4:28 $200 of cash flow a month every 4:30 transaction. If you're trying to get to 4:32 $10,000 a month or more, you're going to 4:34 have to buy again and again and again 4:37 and again and again. And one disaster 4:40 happens at one property, it can wipe out 4:41 most of your cash flow. So single family 4:44 doesn't work for a series of reasons. 4:47 Too many transactions to get from A to 4:49 B. The competition's wrong. And it's a 4:51 business that's not designed to be a 4:53 business. you are taking a normal single 4:55 family residence and trying to make more 4:58 money off it. Here's the case for multif 5:00 family and why I really like this or if 5:02 you want to do the short-term rental 5:03 thing, why you should do boutique hotel 5:05 as opposed to the individual Airbnb. 5:09 It's easy to get in the mindset of, 5:10 well, it costs less money, so it's 5:12 easier for me to get in. I'm going to 5:14 dispel that right now. The bigger the 5:15 deal, typically the easier the raises. 5:17 until you get into the multi-million 5:19 dollar raises, 5:20 it's more attractive for more people to 5:22 invest in something that's bigger than 5:24 they can do on their own. So, your 5:26 actual ability to buy these low to no 5:28 money out of pocket is going to increase 5:30 dramatically. And again, boutique hotel 5:32 and midsize multif family. We're talking 5:34 five to 50 units. We're not talking 5:37 Titanic properties. We're not talking 5:38 the 300 unit mega complex that just got 5:41 built right down the street. We're 5:43 talking about something built in the 5:45 80s, 90s, early 2000s. It's five to, you 5:48 know, 50 units at the most. That is a 5:52 sweet spot where you can operate. It's 5:54 low capital raises. It's not capital 5:56 intensive. You can attract investors, 5:58 too. And it's designed very specifically 6:01 to cash flow. So, that's argument number 6:04 one. Buy bigger will actually make it 6:06 easier. So, if you're stuck in the 6:07 mindset of like, well, it costs less, so 6:09 it's easier to obtain. I need to find 6:11 less money. Stop doing that immediately. 6:13 You create an opportunity. That 6:15 opportunity, the cash flow and the 6:17 upside of the actual opportunity is what 6:19 attracts capital. In my experience, and 6:21 I do have a good deal over the last 32 6:23 transactions, it is much easier to raise 6:26 a million dollars for a fantastic cash 6:28 flowing deal than a speculative single 6:30 family house. Your investor pool is 6:32 actually much larger. A million dollars 6:34 in multif family, much easier to find 6:37 than $100,000 in single family. So, 6:39 that's my first piece of advice for you. 6:41 Second, it's the scalability. I only 6:43 need to succeed about once a quarter. 6:45 And really, twice a year would still do 6:47 it. If you bought a couple of 25 unit 6:49 buildings and each of these cash flow 6:52 three $4,000 a month, you add $8,000 a 6:55 month for life and it adjusts with 6:57 inflation. So, every year it goes up a 6:58 little bit over time on average. You do 7:01 very very well here. But if two 7:03 transactions can get me to eight n 7:05 $10,000 a month, and I do this every 7:08 single year consistently, 7:11 once every half year, once every 7:12 quarter, maybe up to four deals, you 7:15 start accumulating hundreds of rental 7:17 units without doing a lot of volume. the 7:19 sustainability of this, the management 7:21 of this, the systems, you can build a 7:23 business that spits out tens of 7:24 thousands of dollars instead of scraping 7:27 your way to your next five or 10 7:29 thousand dollars over multiple years 7:30 with tons of transactions and a lot of 7:32 headache. My last argument, negotiating 7:36 deals, single family, you tend to get a 7:39 whole lot of problems in the small 7:41 properties buying from the small momand- 7:44 pop owners. They're usually selling 7:46 because there's some problem with the 7:47 property. They bought it to be passive. 7:49 They run it incorrectly. It's not 7:51 passive at all. You're coming in and 7:52 fixing substantial problems. That's a 7:54 majority of the deals we see. So, you 7:56 have to push the margin by building an 7:58 ADU. So, you have to be a little micro 8:00 developer or you have to switch the use 8:03 to Airbnb and spend the time, money, and 8:05 risk to get it there. On multif family, 8:07 you are negotiating the deals based on 8:09 the cash flow today and the future 8:11 upside, which is just a factor of how 8:13 well you run the property. The 8:15 appraisals are done on your net 8:17 operating income, not on what your 8:19 neighbors just sold their property for. 8:21 So, your ability to find debt products, 8:23 to find capital, the transaction volume, 8:25 everything is easier. And at the end of 8:26 the day, walk around a 25 unit building 8:30 or a 50unit building. The feeling you 8:33 get being like, I own this versus 8:35 walking in front of a random house 8:37 somewhere that you'll probably never go 8:38 in again. It's a different feeling. It's 8:41 a bigger business. you it's more 8:44 rewarding and ultimately you're 8:46 providing housing to people who want to 8:48 rent. You're not taking homes off the 8:50 market. You're not competing with 8:51 everyone else. So hopefully those five 8:53 or six reasons is enough to change your 8:55 mind if you're looking at single family 8:56 to go, "Hey, this year, right now I'm 8:59 filming this in 2026, right in the 9:01 beginning of 2026. 9:03 If you're sitting here going like, "Hey, 9:04 2026 is my year to dive into real estate 9:05 and I think I'm going to go buy my first 9:07 investment house." Here's my challenge 9:08 to you. Increase it by five units. Do 9:11 something commercial. It doesn't have to 9:12 be huge. Buy a 5plex, buy a 12plex, 9:15 do a slightly larger property where 9:17 you're going to find easier to manage, 9:19 more availability, more cash flow, 9:21 easier to find the money, easier to 9:23 close, and easier to manage. Hope this 9:27 [music] helps. I'll see you guys on the 9:29 next episode.
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